WO2022040002A1 - Methods and compositions for targeting pd-l1 - Google Patents

Methods and compositions for targeting pd-l1 Download PDF

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Publication number
WO2022040002A1
WO2022040002A1 PCT/US2021/045696 US2021045696W WO2022040002A1 WO 2022040002 A1 WO2022040002 A1 WO 2022040002A1 US 2021045696 W US2021045696 W US 2021045696W WO 2022040002 A1 WO2022040002 A1 WO 2022040002A1
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Prior art keywords
compound
alkyl
group
monocyclic
membered
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English (en)
French (fr)
Inventor
Tongfei Wu
Pierre Jean-Marie Bernard Raboisson
Francois GONZALVEZ
Antitsa Dimitrova Stoycheva
Jerome Deval
Cheng Liu
Qingling Zhang
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Aligos Therapeutics Inc
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Aligos Therapeutics Inc
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Priority to EP21858851.5A priority Critical patent/EP4185569B1/en
Priority to CA3190154A priority patent/CA3190154A1/en
Priority to AU2021329259A priority patent/AU2021329259A1/en
Priority to CN202180062965.1A priority patent/CN116209663A/zh
Priority to JP2023512031A priority patent/JP2023539463A/ja
Priority to KR1020237008638A priority patent/KR20230059801A/ko
Publication of WO2022040002A1 publication Critical patent/WO2022040002A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/18—Oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Definitions

  • alkyl groups include, but are in no way limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, pentyl and hexyl.
  • the alkyl group may be substituted or unsubstituted.
  • alkenyl refers to an alkyl group that contains in the straight or branched hydrocarbon chain one or more double bonds.
  • the length of an alkenyl can vary.
  • the alkenyl can be a C2-4 alkenyl, C2-6 alkenyl or C2-8 alkenyl.
  • alkenyl groups include allenyl, vinylmethyl and ethenyl.
  • alkoxy refers to the formula –OR wherein R is an alkyl, an alkenyl, an alkynyl, a cycloalkyl, a cycloalkenyl, aryl, heteroaryl, heterocyclyl, aryl(alkyl), heteroaryl(alkyl) or heterocyclyl(alkyl) is defined herein.
  • Embodiment 16 [0089] The compound of Embodiment 13 or 14; wherein R 4a3 can be –NR p1 R q1 .
  • Embodiment 17 [0090] The compound of any one of Embodiments 13-16, wherein R 5a3 and R 5b3 can be each hydrogen.
  • Embodiment 18 [0091] The compound of any one of Embodiment 7-11, wherein R 7a2 can be –C 1-4 haloalkyl (such as -CHF 2 and -CF 3 ).
  • Embodiment 59 [0132] The compound of Embodiment 57, wherein R Z4 can be hydrogen or –C 1-4 alkyl.
  • Embodiment 60 [0133] The compound of Embodiment 57, wherein R 2a4 can be –NH(R m3 ), wherein R m3 can be selected from –C 1-4 alkyl and –C 3-6 monocyclic cycloalkyl.
  • Embodiment 97 [0170] The compound of Embodiment 1 selected from: O , , , , , ,
  • Step 2 A mixture of Intermediate 12 (400 mg, 1.46 mmol), Intermediate 4 (1.04 g, 2.19 mmol), Pd(dppf)Cl2 (107mg, 146 ⁇ mol), K2CO3 (605 mg, 4.38 mmol) in dioxane (20 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 95 °C for 16 h under N 2 atmosphere.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Virology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/US2021/045696 2020-08-17 2021-08-12 Methods and compositions for targeting pd-l1 Ceased WO2022040002A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP21858851.5A EP4185569B1 (en) 2020-08-17 2021-08-12 Methods and compositions for targeting pd-l1
CA3190154A CA3190154A1 (en) 2020-08-17 2021-08-12 Methods and compositions for targeting pd-l1
AU2021329259A AU2021329259A1 (en) 2020-08-17 2021-08-12 Methods and compositions for targeting PD-L1
CN202180062965.1A CN116209663A (zh) 2020-08-17 2021-08-12 用于靶向pd-l1的方法和组合物
JP2023512031A JP2023539463A (ja) 2020-08-17 2021-08-12 Ｐｄ－ｌ１を標的とするための方法及び組成物
KR1020237008638A KR20230059801A (ko) 2020-08-17 2021-08-12 Pd-l1을 표적화하기 위한 방법 및 조성물

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US202063066689P 2020-08-17 2020-08-17
US63/066,689 2020-08-17
US202163210423P 2021-06-14 2021-06-14
US63/210,423 2021-06-14

Publications (1)

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WO2022040002A1 true WO2022040002A1 (en) 2022-02-24

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PCT/US2021/045696 Ceased WO2022040002A1 (en) 2020-08-17 2021-08-12 Methods and compositions for targeting pd-l1

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US (1) US11760761B2 (https=)
EP (1) EP4185569B1 (https=)
JP (1) JP2023539463A (https=)
KR (1) KR20230059801A (https=)
CN (1) CN116209663A (https=)
AU (1) AU2021329259A1 (https=)
CA (1) CA3190154A1 (https=)
TW (1) TW202227451A (https=)
WO (1) WO2022040002A1 (https=)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115232109A (zh) * 2021-04-25 2022-10-25 广东东阳光药业有限公司 Pd-1/pd-l1类小分子抑制剂及其在药物中的应用
WO2022266236A1 (en) * 2021-06-18 2022-12-22 Aligos Therapeutics, Inc. Methods and compositions for targeting pd-l1
US11760764B2 (en) 2020-05-22 2023-09-19 Aligos Therapeutics, Inc. Methods and compositions for targeting PD-L1
US11851422B2 (en) 2021-07-09 2023-12-26 Aligos Therapeutics, Inc. Anti-viral compounds
WO2024134466A1 (en) * 2022-12-21 2024-06-27 Arbutus Biopharma Corporation Substituted arylamine compounds, substituted heteroarylamine compounds, and methods using same
US12065428B2 (en) 2021-09-17 2024-08-20 Aligos Therapeutics, Inc. Anti-viral compounds
WO2024175043A1 (zh) * 2023-02-23 2024-08-29 广东东阳光药业股份有限公司 吡啶并嘧啶衍生物及其用途
WO2025015063A1 (en) * 2023-07-13 2025-01-16 Aligos Therapeutics, Inc. Methods and compositions for targeting pd-l1
WO2025171025A1 (en) * 2024-02-07 2025-08-14 Aligos Therapeutics, Inc. Pd-l1 compounds with a bicyclic group
WO2025171031A1 (en) * 2024-02-07 2025-08-14 Aligos Therapeutics, Inc. Pd-l1 compounds with a bicyclic group
WO2025174835A1 (en) * 2024-02-15 2025-08-21 Aligos Therapeutics, Inc. Methods and compositions for targeting pd-l1
WO2025199273A1 (en) * 2024-03-22 2025-09-25 Aligos Therapeutics, Inc. Methods and compositions for targeting pd-l1
WO2025199281A1 (en) * 2024-03-22 2025-09-25 Aligos Therapeutics, Inc. Methods and compositions for targeting pd-l1
US12428427B2 (en) 2021-12-16 2025-09-30 Aligos Therapeutics, Inc. Methods and compositions for targeting PD-L1

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JP2023539463A (ja) 2023-09-14
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US11760761B2 (en) 2023-09-19
KR20230059801A (ko) 2023-05-03
AU2021329259A1 (en) 2023-03-02
US20230065527A1 (en) 2023-03-02
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CA3190154A1 (en) 2022-02-24
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